Potassium Carbonate → HCID 73438561, compound

HRID 2166978Notes

Reaction equation

HRID 2166978 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13](Cl)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:20](=O)([O-])[O-].[K+].[K+].[NH2:26][C:27]1[C:40]([Cl:41])=[CH:39][C:38]([Cl:42])=[CH:37][C:28]=1[C:29]([N:31]=[S:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[O:30]>C(#N)C>[CH:27]([O:14][CH:13]([CH3:12])[CH3:20])([CH3:40])[CH3:28].[Cl:42][C:38]1[CH:39]=[C:40]([Cl:41])[C:27]([NH:26][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[O:14])=[C:28]([C:29](=[O:30])[N:31]=[S:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH:37]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl ChlorideHCID 86720247HCID 86720247, compound

Product 2

HCID 7914Diisopropyl EtherHCID 73438561HCID 73438561, compoundYield 173.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carbonyl chloride (210.7 g, 0.68 mol, 1.10 equiv.) in acetonitrile (500 mL) was added at 22° C. to a suspension of potassium carbonate (103.34 g, 0.74 mol, 1.20 equiv) and 2-amino-3,5-dichloro-N-(diethyl-λ4-sulfanylidene)-benzamide (181.79 g, 0.62 mol, 1.00 equiv) in acetonitrile (2 L). After 2.5 h at this temperature, the reaction mixture was poured into ice-water with stirring. The resulting precipitate was collected by filtration and washed with water and petrol ether. Trituration from diisopropyl ether yielded the crystalline title compound (305 g, 87%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water and petrol ether

Sources & evidence

ORD record
ord-5d266f1eb761402bba36de03b44fb2db
Source dataset
uspto-grants-2015_06
Patent number
US09044016B2

Reaction notes

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